If rules were made to be broken, why are so many of us so afraid of breaking them?

They have their function, after all: if everyone took a red light as but a minor suggestion, driving—or merely riding in—a car would be a seriously risky endeavor. Actually though, it occurs to me as I type this, there’s an intersection by my house, near where I get onto the freeway to go North. The light works on some sort of timer or sensor or something. And several times, in the painfully early hours when I’ve been on my way to the airport, I’ve sat at that light. And I’ve waited. And waited. And waited. In fact, I’ve never seen it turn green. More than once I’ve inched into that intersection, staring down the deserted streets, thinking to myself “Should I, or shouldn’t I?”

I got to thinking about all this rule-breaking business after hearing Barry Schwartz’ most recent TED Talk on NPR. In it, he talks about what he calls “practical wisdom,” how ideas and behaviors that typically would fall under the heading of “common sense” are valued less and less. His talk focused primarily on organizations and institutions, how an over-reliance on policies and procedures creates bureaucracies and red tape the navigation of which take precedence over a more thoughtful approach–and which are a nightmare to deal with, to boot. How we can get so focused on objective knowledge that our humanity takes a hit. How sometimes, in fact, the rules can lead us astray – as when one man’s child was taken from him after a security guard spotted the clueless father giving his son a Hard Lemonade at a baseball game, oblivious to the fact that “hard” meant booze. Though it was an honest mistake, it was weeks before the child was returned to his home and his father allowed to see him again.

What’s all this got to do with the rest of us? I tend to think quite a bit. When it comes to what we choose to do with our lives—and the angst around those choices—I’d bet that no small part of the difficulty there has to do with the tension between the desire to be true to ourselves, and the desire to play by the rules. To do the things that are expected of us. To color within the lines. To be the perfect fill-in-the-blank. (And the perfect fill-in-the-other-blank, and the other blank, and the other blank…) Certain things are allowed. Certain things are expected. But are they right? And, more importantly, are they right for us? How can we be sure?

Schwartz quotes Aristotle, saying that practical wisdom is figuring out the right way to do the right thing in a particular circumstance, with a particular person, at a particular time. In other words, it’s subjective. Frustratingly so… except when you consider that, if that’s the goal–to live with practical wisdom–you have all the answers you need. You don’t need to consult the rule book—or bow down to the shoulds—because the only should that matters is that you do what’s right for you, given the circumstances of your life now. If that means coloring outside of the lines, so be it. In fact, if that means coloring outside of the lines, then that’s exactly what you should do.